20,29-epoxy-6β-hydroxy-3-oxolupan-28-oic acid | 877315-43-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 20,29-epoxy-6β-hydroxy-3-oxolupan-28-oic acid
• 英文别名: (1R,3aS,5aR,5bR,7R,7aR,11aR,11bR,13aR,13bS)-7-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(2-methyloxiran-2-yl)-9-oxo-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1H-cyclopenta[a]chrysene-3a-carboxylic acid
• CAS: 877315-43-0
• 化学式: C₃₀H₄₆O₅
• 分子量: 486.692
• InChiKey: NBRUEFVVSUEORD-VXLYBVKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  35
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  87.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  20,29-epoxy-6β-hydroxy-3-oxolupan-28-oic acid 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 72.0h， 以50.5 mg的产率得到6β,30-dihydroxy-3-oxolup-20(29)-en-28-oic acid
  参考文献：
  名称：

  Lupane and Oleanane Triterpenoids from the Cones of Liquidamber styraciflua

  摘要：

  A new lupane- (1) and a new oleanane-type (2) triterpenoid, together with a known compound, massagenic acid G, were isolated from the cones of Liquidamber styraciflua. The structures of 1 and 2 were determined as 6 beta,30-dihydroxy-3-oxolup-20(29)-en-28-oic acid and 3 alpha-hydroxy-11-oxoolean-12-en-28-oic acid, respectively, on the basis of spectroscopic methods and chemical conversion. Compound 1 and several structural analogues were evaluated for cytotoxicity against the P388 (murine lymphocyte leukemia) and the A549 (human lung cancer) cell lines.

  DOI：

  10.1021/np0581014
• 作为产物：
  描述：

  6β-hydroxy-3-oxolup-20(29)-en-28-oic acid 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以507.6 mg的产率得到20,29-epoxy-6β-hydroxy-3-oxolupan-28-oic acid
  参考文献：
  名称：

  Lupane and Oleanane Triterpenoids from the Cones of Liquidamber styraciflua

  摘要：

  A new lupane- (1) and a new oleanane-type (2) triterpenoid, together with a known compound, massagenic acid G, were isolated from the cones of Liquidamber styraciflua. The structures of 1 and 2 were determined as 6 beta,30-dihydroxy-3-oxolup-20(29)-en-28-oic acid and 3 alpha-hydroxy-11-oxoolean-12-en-28-oic acid, respectively, on the basis of spectroscopic methods and chemical conversion. Compound 1 and several structural analogues were evaluated for cytotoxicity against the P388 (murine lymphocyte leukemia) and the A549 (human lung cancer) cell lines.

  DOI：

  10.1021/np0581014